Phosphorus oxychloride → 4-Chloropyrrolo(2,1-f)(1,2,4)triazine

Temperature

100 °C

To a solution of pyrrolo[2,1-f][1,2,4]triazin-4-ol (3.70 g, 27.4 mmol, see generally, PCT Appl. WO 2000/071129 the disclosure of which is herein incorporated by reference in its entirety) in 40 mL of toluene at room temperature was added 4.77 mL (27.4 mmol) of diisopropylethylamine followed by 7.70 mL (82.6 mmol) of phosphorus oxychloride. The reaction mixture was heated at 100° C. for 18 h. After cooling to room temperature, the reaction was slowly added to a solution of 5% aq NaHCO3 solution (100 mL) at 0° C. Upon completion of the addition, the biphasic mixture was allowed to stir at room temperature for 30 min. The aqueous layer was extracted with EtOAc (3×100 mL) and the pooled organic extracts were washed with brine (100 mL), dried over anhydrous MgSO4, and concentrated in vacuo to give the crude product (4.10 g, 97%) as a yellow solid. 1H NMR (CDCl3) δ 8.14 (s, 1H), 7.80 (dd, 1H, J=2.4, 1.5 Hz), 6.91 (m, 2H).

1. customat room temperature
2. temperatureAfter cooling to room temperature
3. additionUpon completion of the addition
4. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
5. washthe pooled organic extracts were washed with brine (100 mL)
6. dry with materialdried over anhydrous MgSO4
7. concentrationconcentrated in vacuo

ORD record

ord-7b64f63f4cd0480f90b4e0e19262f562

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07173031B2